4-Chloro-N-(3-methyl­benzo­yl)benzene­sulfonamide monohydrate

P A Suchetan; Sabine Foro; B Thimme Gowda; M Shet Prakash

doi:10.1107/S1600536811051932

. 2011 Dec 7;68(Pt 1):o46. doi: 10.1107/S1600536811051932

4-Chloro-N-(3-methylbenzoyl)benzenesulfonamide monohydrate

P A Suchetan ^a, Sabine Foro ^b, B Thimme Gowda ^a,^*, M Shet Prakash ^c

PMCID: PMC3254406 PMID: 22259549

Abstract

In the title compound, C₁₄H₁₂ClNO₃S·H₂O, the dihedral angle between the sulfonyl and benzoyl benzene rings is 84.4 (2)°. In the crystal, every water molecule forms four hydrogen bonds with three different molecules of 4-chloro-N-(3-methylbenzoyl)benzenesulfonamide. One of the water H atoms forms a bifurcated hydrogen bond with both the sulfonyl and the carbonyl O atoms of the same molecule. Molecules are linked into layers in the ab plane through N—H⋯O and O—H⋯O hydrogen bonds.

Related literature

For our studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Gowda et al. (2004 ▶), on N-(aryl)-methanesulfonamides, see: Jayalakshmi & Gowda (2004 ▶), on N-(aryl)-arylsulfonamides, see: Gowda et al. (2003 ▶), on N-(substitutedbenzoyl)-arylsulfonamides, see: Suchetan et al. (2011 ▶) and on N-chloroarylamides, see: Gowda et al. (1996 ▶).

Experimental

Crystal data

C₁₄H₁₂ClNO₃S·H₂O
M _r = 327.77
Orthorhombic,
a = 5.0148 (6) Å
b = 12.864 (2) Å
c = 46.314 (5) Å
V = 2987.7 (7) Å³
Z = 8
Mo Kα radiation
μ = 0.41 mm⁻¹
T = 293 K
0.46 × 0.14 × 0.06 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T _min = 0.834, T _max = 0.976
5972 measured reflections
2684 independent reflections
1959 reflections with I > 2σ(I)
R _int = 0.037

Refinement

R[F ² > 2σ(F ²)] = 0.105
wR(F ²) = 0.185
S = 1.35
2684 reflections
200 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811051932/bt5739sup1.cif

e-68-00o46-sup1.cif^{(18.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811051932/bt5739Isup2.hkl

e-68-00o46-Isup2.hkl^{(131.9KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811051932/bt5739Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O4	0.86 (2)	1.93 (2)	2.771 (8)	169 (6)
O4—H41⋯O1ⁱ	0.84 (2)	2.29 (7)	2.916 (7)	131 (8)
O4—H41⋯O3ⁱ	0.84 (2)	2.42 (6)	3.117 (8)	140 (8)
O4—H42⋯O2ⁱⁱ	0.84 (2)	2.35 (6)	3.022 (8)	137 (8)

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

BTG thanks the University Grants Commission, Government of India, New Delhi, for a special grant under the UGC–BSR one-time grant to faculty.

supplementary crystallographic information

Comment

Diaryl acylsulfonamides are known as potent antitumor agents. As part of our studies on the substituent effects on the structures and other aspects of N-(aryl)-amides (Gowda et al., 2004), N-(aryl)-methanesulfonamides (Jayalakshmi & Gowda, 2004), N-(aryl)-arylsulfonamides (Gowda et al., 2003); N-(substitutedbenzoyl)-arylsulfonamides (Suchetan et al., 2011) and N-chloro-arylsulfonamides (Gowda et al., 1996), in the present work, the crystal structure of 4-Chloro-N-(3-methylbenzoyl)-benzenesulfonamide monohydrate (I) has been determined (Fig.1).

The conformations of the N—H and C=O bonds in the C—SO₂—NH—C(O) segment are anti to each other (Fig.1), similar to that observed in 4-Chloro-N-(2-methylbenzoyl)-benzenesulfonamide monohydrate (II) (Suchetan et al., 2011). The molecule is twisted at the S- atom with the torsional angle of -70.67 (55)°, compared to the value of -69.2 (2)° in (II).

The dihedral angle between the sulfonyl benzene ring and the —SO₂—NH—C—O segment is 78.4 (2)°, compared to the value of 87.2 (1)° in (II). Furthermore, the dihedral angle between the sulfonyl and the benzoyl benzene rings is 84.4 (2)°, compared to the value of 57.7 (1)° in (II).

Further, the crystal structure shows interesting H-bonding. Every water molecule forms four H-bonds with three different molecules of the title compound. One of the H-atoms of the water molecule forms simultaneous H-bonding with both the sulfonyl and the carbonyl oxygen atoms of the same molecule.

The packing of molecules through N1—H1N···O4, O4—H41···O1, O4—H41···O3 and O4—H42···O2 hydrogen bonds (Table 1) is shown in Fig. 2.

Experimental

The title compound was prepared by refluxing a mixture of m-methyl benzoic acid (0.02 mole), 4-chlorobenzenesulfonamide (0.02 mole) and excess phosphorous oxy chloride for 3 h on a water bath. The resultant mixture was cooled and poured into crushed ice. The solid, 4-Chloro-N-(3-methylbenzoyl)-benzenesulfonamide monohydrate, obtained was filtered, washed thoroughly with water and then dissolved in sodium bicarbonate solution. The compound was later reprecipitated by acidifying the filtered solution with dilute HCl. It was filtered, dried and recrystallized.

Needle like colourless single crystals of the title compound used in X-ray diffraction studies were obtained by slow evaporation of its ethanol-tetrahydrofuran solution at room temperature.